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Most people I work with don’t know this about me, because I make sure it all stays in the background, but to be blunt, I’m kind of the perfect person to address a cognitive bias called the “planning fallacy, because I’m an expert in it. I should get sponsorships from the planning fallacy. I could be its brand partner.

If memory serves, I once wrote 10 pages of a college paper the morning it was due. I often pack the day of a trip (sometimes within half an hour or less of when I need to leave). When I was little, I’d procrastinate practicing the piano until about a week or two before a recital, when I’d have to learn, memorize, and hone half or more of a Chopin nocturne in an unnecessary warp-speed frenzy.

Although I’ve never missed a flight, my train record is not impeccable, and, on a not-insignificant portion of my trips, I’ve arrived at my seat…let’s call it glistening. It’s not unusual for me to be finishing the last few pages of my book club’s book in the last few minutes before the meeting. And yet, I’m often surprised to find myself in this situation.

I’ll admit: rushing does sometimes energize me, deadlines motivate me, and more often than not, I pull it off—but with so much more glistening than necessary. (Don’t worry, showers are taken in the aftermath of the glistening.)

These dances (if you can call my trotting awkwardly up the platform of Union Station while my small roll-y suitcase cries “uncle” behind me a dance) make for funny stories, but only because they didn’t involve messing up a big presentation or letting someone on my team down. In other words, they’re fine if the stakes are relatively low. If not, they can harm your business and career. Humans vary in the degree to which they fall prey to the planning fallacy, but it is a recognized and prominent psychological hurdle.

WHAT IS THE PLANNING FALLACY?

The planning fallacy observes that we often lowball our prediction of the length of time an activity will take, even—and here’s the kicker—if we’ve done something similar to it in the past. In other words, we should know better!

What does this look like in sales? It can be thinking a deal is near closing when, in reality, you miscalculated just how long it would sit in legal. Or failing to properly time a demo to account for questions a prospect may have throughout the presentation.

HOW DO WE PROTECT OUR SALES PROCESS?

1. Know the steps
   What are the vital things that need to be finalized in order to progress a deal? Equally important, know when they need to be finalized. What (and how long) does procurement approval look like for this particular client?
   
2. Anticipate holdups
   Know which junctures tend to create a time bottleneck. A great way to do this? Think about previous experiences with a deal similar to this one—or ask colleagues, mentors, and other resources to gain some insight into experiences you haven’t yet had.
   
3. Know which timelines are flexible
   Certain assignments within a project have a domino effect and can risk delaying closing a deal if they themselves are delayed. If you’ve taken Maestro’s Velocity training. In that case, you know that it’s vital to distinguish between an item that may stretch your sales cycle, like legal review, and those that may not, such as technical review for a technically straightforward service.
   
4. Make a plan
   Call it a mutual action plan (MAP), a closing schedule, or a Boss-ter roster (don’t call it that), but make sure you have one. This includes important tasks or milestones and the dates by which they need to be accomplished. It should also include who “owns” the task.
   
5. Distrust your plan
   That might be putting it a little dramatically, but this basically means: do not forget about the planning fallacy. Rather, give yourself a time cushion.
   
6. Use a CRM
   A CRM will allow you and your team to easily consult previous deals and recall how long their subparts took. This will let you pad your schedule appropriately, plan with confidence, and hold yourself accountable, so that each step happens when it’s supposed to.

WE KNOW…

A lot of this may sound basic. Building in extra time is not rocket science. Having a plan and clarifying everyone’s role in it do not make for a good game-show premise. CRMs? Not always thrilling. And still, these are the types of things that Maestro has seen improve company outcomes innumerable times. (Well, not innumerable, because they’re probably in the CRM.) So, after you’ve planned, assume something will take longer than you think it will. In short, do not underestimate your ability to underestimate.

If you’re interested in Maestro’s Velocity training or any of the other deep dives into the DRIVE Information Gathering Framework, you can get them here for free!